CN101481343A - Method for synthesizing N,N-diethylamino ethanethiol - Google Patents
Method for synthesizing N,N-diethylamino ethanethiol Download PDFInfo
- Publication number
- CN101481343A CN101481343A CNA2009103004732A CN200910300473A CN101481343A CN 101481343 A CN101481343 A CN 101481343A CN A2009103004732 A CNA2009103004732 A CN A2009103004732A CN 200910300473 A CN200910300473 A CN 200910300473A CN 101481343 A CN101481343 A CN 101481343A
- Authority
- CN
- China
- Prior art keywords
- diethylamino ethanethiol
- synthetic method
- diethylamine
- ethanethiol
- diethylamino
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims abstract description 12
- JOBAOCJQNOWKPH-UHFFFAOYSA-N 1-(diethylamino)ethanethiol Chemical compound CCN(CC)C(C)S JOBAOCJQNOWKPH-UHFFFAOYSA-N 0.000 title abstract 3
- 230000002194 synthesizing effect Effects 0.000 title 1
- 238000006243 chemical reaction Methods 0.000 claims abstract description 26
- VOVUARRWDCVURC-UHFFFAOYSA-N thiirane Chemical compound C1CS1 VOVUARRWDCVURC-UHFFFAOYSA-N 0.000 claims abstract description 22
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims abstract description 20
- 238000010189 synthetic method Methods 0.000 claims abstract description 17
- 239000003054 catalyst Substances 0.000 claims abstract description 4
- 238000002156 mixing Methods 0.000 claims abstract description 3
- YBDSNEVSFQMCTL-UHFFFAOYSA-N 2-(diethylamino)ethanethiol Chemical compound CCN(CC)CCS YBDSNEVSFQMCTL-UHFFFAOYSA-N 0.000 claims description 12
- 238000010992 reflux Methods 0.000 claims description 9
- 230000000630 rising effect Effects 0.000 claims description 9
- 238000004821 distillation Methods 0.000 claims description 7
- 238000003756 stirring Methods 0.000 claims description 7
- 150000002170 ethers Chemical class 0.000 claims description 6
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 5
- 239000012279 sodium borohydride Substances 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 2
- 238000006116 polymerization reaction Methods 0.000 abstract description 6
- 239000002904 solvent Substances 0.000 abstract description 4
- 239000002994 raw material Substances 0.000 abstract description 3
- 239000002699 waste material Substances 0.000 abstract description 3
- 238000010438 heat treatment Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 description 11
- 238000005516 engineering process Methods 0.000 description 5
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
- -1 sulphur hydrogen salt Chemical class 0.000 description 3
- 239000005864 Sulphur Substances 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- PQLFROTZSIMBKR-UHFFFAOYSA-N ethenyl carbonochloridate Chemical compound ClC(=O)OC=C PQLFROTZSIMBKR-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- UURAUHCOJAIIRQ-QGLSALSOSA-N tiamulin Chemical compound CCN(CC)CCSCC(=O)O[C@@H]1C[C@@](C)(C=C)[C@@H](O)[C@H](C)[C@@]23CC[C@@H](C)[C@]1(C)[C@@H]2C(=O)CC3 UURAUHCOJAIIRQ-QGLSALSOSA-N 0.000 description 2
- 229960004885 tiamulin Drugs 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- ZXYFGZNMDRNOGQ-UHFFFAOYSA-N ac1lawgt Chemical compound [S]O ZXYFGZNMDRNOGQ-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
Claims (10)
- [claim 1] a kind of N, the synthetic method of N-diethylamino ethanethiol is characterized in that: this method comprises: under the condition that adds catalyzer, after thiirane and diethylamine mixing, be heated to 50 ℃~80 ℃ reactions and make N, the N diethylamino ethanethiol.
- [claim 2] N according to claim 1, the synthetic method of N-diethylamino ethanethiol, it is characterized in that: elder generation adds thiirane and stirs in reaction unit, after adding diethylamine and catalyzer again, it is stirred, and can make N, the N-diethylamino ethanethiol in 50 ℃~80 ℃ following temperature rising reflux reactions.
- [claim 3] N according to claim 2, the synthetic method of N-diethylamino ethanethiol is characterized in that: after the reaction of stirring temperature rising reflux finished, diethylamine and catalyzer were reclaimed in distillation, and underpressure distillation can make N again, the N diethylamino ethanethiol.
- [claim 4] N according to claim 3, the synthetic method of N-diethylamino ethanethiol is characterized in that: described reaction unit is a reactor.
- [claim 5] N according to claim 3, the synthetic method of N-diethylamino ethanethiol is characterized in that: the reaction times of described temperature rising reflux is 10 hours~15 hours.
- According to the arbitrary described N of claim 1~3, the synthetic method of N-diethylamino ethanethiol is characterized in that [claim 6]: the consumption of described thiirane is 1:1~1:10 with the ratio of the consumption of diethylamine.
- According to the arbitrary described N of claim 1~3, the synthetic method of N-diethylamino ethanethiol is characterized in that [claim 7]: described catalyzer is a boiling point greater than 60 ℃ ethers.
- [claim 8] N according to claim 7, the synthetic method of N-diethylamino ethanethiol is characterized in that: described ethers is a sherwood oil.
- According to the arbitrary described N of claim 1~3, the synthetic method of N-diethylamino ethanethiol is characterized in that [claim 9]: described catalyzer is a sodium borohydride.
- According to the arbitrary described N of claim 1~3, the synthetic method of N-diethylamino ethanethiol is characterized in that [claim 10]: described catalyst consumption is to account for 0.5%~10% of thiirane and diethylamine total mass.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN200910300473A CN100593537C (en) | 2009-02-18 | 2009-02-18 | Method for synthesizing N,N-diethylin ethanethiol |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN200910300473A CN100593537C (en) | 2009-02-18 | 2009-02-18 | Method for synthesizing N,N-diethylin ethanethiol |
Publications (2)
Publication Number | Publication Date |
---|---|
CN101481343A true CN101481343A (en) | 2009-07-15 |
CN100593537C CN100593537C (en) | 2010-03-10 |
Family
ID=40878656
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN200910300473A Active CN100593537C (en) | 2009-02-18 | 2009-02-18 | Method for synthesizing N,N-diethylin ethanethiol |
Country Status (1)
Country | Link |
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CN (1) | CN100593537C (en) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102153494A (en) * | 2011-03-04 | 2011-08-17 | 赵云现 | Synthesis technology for N,N-diethylamino group ethanethiol |
CN104774164A (en) * | 2015-02-16 | 2015-07-15 | 张丽学 | Preparation process for 2-diethylaminoethanethiol |
CN105152990A (en) * | 2015-07-30 | 2015-12-16 | 宁夏泰瑞制药股份有限公司 | Preparation method for diethylaminoethanethiol |
CN104447449B (en) * | 2014-12-30 | 2016-06-15 | 陕西师范大学 | The method of one pot process taimulin |
CN112812026A (en) * | 2020-12-30 | 2021-05-18 | 茂名云龙工业发展有限公司 | Method for producing N, N-diethylamino isopropanol |
CN113372248A (en) * | 2021-06-11 | 2021-09-10 | 保定北瑞甾体生物有限公司 | Process for preparing thiols |
CN114315665A (en) * | 2021-12-16 | 2022-04-12 | 保定加合精细化工有限公司 | Preparation method of 2-diethylaminoethanethiol and application of impurities thereof |
-
2009
- 2009-02-18 CN CN200910300473A patent/CN100593537C/en active Active
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102153494A (en) * | 2011-03-04 | 2011-08-17 | 赵云现 | Synthesis technology for N,N-diethylamino group ethanethiol |
CN104447449B (en) * | 2014-12-30 | 2016-06-15 | 陕西师范大学 | The method of one pot process taimulin |
CN104774164A (en) * | 2015-02-16 | 2015-07-15 | 张丽学 | Preparation process for 2-diethylaminoethanethiol |
CN105152990A (en) * | 2015-07-30 | 2015-12-16 | 宁夏泰瑞制药股份有限公司 | Preparation method for diethylaminoethanethiol |
CN105152990B (en) * | 2015-07-30 | 2017-03-22 | 宁夏泰瑞制药股份有限公司 | Preparation method for diethylaminoethanethiol |
CN112812026A (en) * | 2020-12-30 | 2021-05-18 | 茂名云龙工业发展有限公司 | Method for producing N, N-diethylamino isopropanol |
CN113372248A (en) * | 2021-06-11 | 2021-09-10 | 保定北瑞甾体生物有限公司 | Process for preparing thiols |
CN114315665A (en) * | 2021-12-16 | 2022-04-12 | 保定加合精细化工有限公司 | Preparation method of 2-diethylaminoethanethiol and application of impurities thereof |
Also Published As
Publication number | Publication date |
---|---|
CN100593537C (en) | 2010-03-10 |
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C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
EE01 | Entry into force of recordation of patent licensing contract |
Assignee: Baoding Jiahe Fine Chemical Co., Ltd. Assignor: Zhao Yunxian Contract record no.: 2010130000093 Denomination of invention: Light injection and fully internal reflection type 1XN light switch array Granted publication date: 20100310 License type: Exclusive License Open date: 20090715 Record date: 20100831 |
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EC01 | Cancellation of recordation of patent licensing contract |
Assignee: Baoding Jiahe Fine Chemical Co., Ltd. Assignor: Zhao Yunxian Contract record no.: 2010130000093 Date of cancellation: 20150909 |
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LICC | Enforcement, change and cancellation of record of contracts on the licence for exploitation of a patent or utility model | ||
C41 | Transfer of patent application or patent right or utility model | ||
TR01 | Transfer of patent right |
Effective date of registration: 20151102 Address after: 071254, Mancheng County, Mancheng County, Hebei City, Baoding Province Patentee after: BAODING JIUFU BIOCHEMICAL CO., LTD. Address before: 071000 Room 601, Kangtai building, 728 West Yuhua Road, Hebei, Baoding Patentee before: Zhao Yunxian |
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CP01 | Change in the name or title of a patent holder | ||
CP01 | Change in the name or title of a patent holder |
Address after: 071254 Yu Jia Zhuang Xiang Pang Cun, Mancheng County, Baoding City, Hebei Province Patentee after: Hebei Yuanda Jiufu Biotechnology Co.,Ltd. Address before: 071254 Yu Jia Zhuang Xiang Pang Cun, Mancheng County, Baoding City, Hebei Province Patentee before: BAODING JIUFU BIOCHEMICAL Co.,Ltd. |